S-(4-氯苯基)呋喃-2-硫代甲酸酯 | 6310-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: S-(4-氯苯基)呋喃-2-硫代甲酸酯
• 英文名称: S-(4-chlorophenyl) furan-2-carbothioate
• 英文别名: S-p-chlorophenyl thio-2-furoate；furan-2-carbothioic acid S-(4-chloro-phenyl ester)；Furan-2-thiocarbonsaeure-S-(4-chlor-phenylester)
• CAS: 6310-30-1
• 化学式: C₁₁H₇ClO₂S
• 分子量: 238.694
• InChiKey: BOMQECGCHAMJKS-UHFFFAOYSA-N

物化性质

• 沸点：
  326.1±38.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-(4-氯苯基)呋喃-2-硫代甲酸酯 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 p-chlorophenyl dithio-2-furoate
  参考文献：
  名称：

  Aminolysis of aryl dithio-2-thiophenates and dithio-2-furoates in acetonitrile

  摘要：

  The aminolyses of the title substrates with anilines and benzylamines are investigated in acetonitrile. A clean second-order kinetics is obtained with a first-order rate law in the amine concentration, which is uncomplicated by the fast proton transfer step. The large magnitude of rho(z) (rho(1g)) as well as rho(x) (rho(nuc)) together with relatively large positive p(xz) values is consistent with a stepwise mechanism in which thiophenolate ion expulsion from the intermediate is rate limiting. For the reactions of aryl dithio-2-thiophenates with benzylamines the magnitude of rho(x) and rho(z) values is relatively smaller suggesting that both the addition and expulsion of thiophenolate are partially rate determining. Relatively large secondary kinetic isotope effects, k(H)/k(D) greater than or equal to 1.7, with deuterated nucleophiles, support involvement a concurrent proton transfer to the departing thiophenolate ion in the transition state. (C) 1998 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1998)30:11<849::aid-kin7>3.0.co;2-v
• 作为产物：
  描述：

  2-甲基呋喃 、 4-氯苯硫酚 在 叔丁基过氧化氢 、 iron(II) bromide 作用下， 以 水 为溶剂， 反应 12.0h， 以48%的产率得到S-(4-氯苯基)呋喃-2-硫代甲酸酯
  参考文献：
  名称：

  铁催化甲基芳烃在水中与硫醇的硫酯化反应

  摘要：

  已经开发了铁催化的甲基芳烃与硫醇的偶联反应，从而生成硫酯。反应在水中以氢过氧化叔丁基（TBHP）为氧化剂，以聚环氧乙烷基α-生育酚癸二酸酯（PTS）为表面活性剂进行。反应介质与一系列官能团相容，可以重复使用。

  DOI：

  10.1016/j.tetlet.2014.10.155

文献信息

• Direct oxidative coupling of thiols and benzylic ethers via C(sp³)–H activation and C–O cleavage to lead thioesters
  作者：J. Feng、M.-F. Lv、G.-P. Lu、C. Cai

  DOI：10.1039/c4ob02250e

  日期：——

  An unprecedented C–S formation method via direct oxidative C(sp3)–H bond functionalization and C–O cleavage of benzylic ethers was developed. Various thioesters including thioester structure containing drug intermediates could be achieved by this convenient, metal and base free method in satisfactory yields.

  通过直接氧化C（sp 3）-H键功能化和苄基醚的C-O裂解，开发了一种前所未有的C-S形成方法。通过这种方便的，无金属和无碱的方法，可以令人满意的产率获得包括含硫酯结构的药物中间体在内的各种硫酯。
• Pt-Catalyzed Regio- and Stereoselective Furylthiolation of Alkynes
  作者：Hitoshi Kuniyasu、Nobuaki Kambe、Takayoshi Hirai、Shigehito Asano、Jun Terao

  DOI：10.1055/s-2005-865232

  日期：——

  The Pt-catalyzed decarbonylative furylthiolation of ­terminal alkynes by furylthioesters took place regio- and stereo­selectively under toluene reflux to give vinylsulfides with cis-furyl group at β-carbon in moderate yields.

  在铂催化下，末端炔烃与巯基呋喃在甲苯回流条件下进行了脱羰基巯基化反应，以中等收率得到了δ-碳上带有顺式呋喃基的乙烯基硫化物。
• Iron-Catalyzed Synthesis of Thioesters from Thiols and Aldehydes in Water
  作者：Yu-Ting Huang、Shao-Yi Lu、Chih-Lun Yi、Chin-Fa Lee

  DOI：10.1021/jo500574p

  日期：2014.5.16

  The preparation of thioesters through the iron-catalyzed coupling reaction of thiols with aldehydes is described. The reactions were carried out by using tert-butyl hydroperoxide (TBHP) as an oxidant and water as a solvent in most cases. This system is compatible with a variety of functional groups.
• Some New Thiol Esters. Preparation of Dithiolfumarates
  作者：Gene Sumrell、Morris Zief、Earl J. Huber、George E. Ham、Charles H. Schramm

  DOI：10.1021/ja01525a052

  日期：1959.8
• Iron-catalyzed thioesterification of methylarenes with thiols in water
  作者：Liang Wang、Jing Cao、Qun Chen、Ming-yang He

  DOI：10.1016/j.tetlet.2014.10.155

  日期：2014.12

  An iron-catalyzed coupling reaction of methylarenes with thiols leading to thioesters has been developed. The reactions were carried out in water with tert-butyl hydroperoxide (TBHP) as the oxidant and polyoxyethanyl α-tocopheryl sebacate (PTS) as the surfactant. The reaction medium is compatible with a series of functional groups and can be reused.

  已经开发了铁催化的甲基芳烃与硫醇的偶联反应，从而生成硫酯。反应在水中以氢过氧化叔丁基（TBHP）为氧化剂，以聚环氧乙烷基α-生育酚癸二酸酯（PTS）为表面活性剂进行。反应介质与一系列官能团相容，可以重复使用。